The word “homeless” applies to different types of people, with different personal stories. The present paper focuses on “handcart dwellers” of the city of S. Paulo. These are people who live on their handcarts, going from one place to another collecting what they can. They are kind of urban nomads, kind of mediaeval traders, itinerants with a moving home. The streets, which are for us, above all, a passing place, are, for them, a living place. For them, the traditional separation between place of work and home – a product of the Industrial Revolution – disappears, in the same way it happened to the post-modern-global-worker that can also be home almost anywhere, thanks to the laptop and the cellular phones. The paper focuses on the notion of space and time of these handcart dwellers, their way of occupation of the city, their spatial and decoration arrangements. As a methodology, both photographic documentation and oral history has been used. This method will shed light onto two aspects of this way of life, both equally significant: the homeless as a product of a wider social, economic and political scenery, which produces and reproduces social exclusion; on the other hand, as subjects who make their acts through singular lines and artefacts.